With the final five underdog Cup Champions, we have a mix of 90s teams and vintage teams from way earlier into the anals of NHL History. These teams were the least likely of all to go all the way and win it all. Let’s get into it!
5. 1990-91 Pittsburgh Penguins
The 1990-91 Pittsburgh Penguins were the benefactors of a lot of luck. They had the most balanced division in the NHL, so finishing first wasn’t overly difficult, which they did, with 88 points on the season. The Penguins beat out the Devils in a hard-fought 7-game series, though it was expected considering the Devils had just 79 points. The Division finals set the Penguins up against the marginally better Washington Capitals, but the Penguins bested them in five games. By far the hardest match for the Penguins came in the Conference final against the Boston Bruins, who’s 100 points were far and above Pittsburgh’s 88-point season. Still, the Penguins persevered and won in a six-game series before taking down the surprise Western finalists in the North Stars in six games.
4. 1948-49 Toronto Maple Leafs
The 1948-49 Maple Leafs are an interesting pick as an underdog team, as they had won their second consecutive Cup just one year prior. However, after a brutally bad regular season, just barely squeaking into the playoffs, the Leafs flipped a switch and became a dominant playoff team. Toronto cruised past the Bruins in five games and then shocked the world by sweeping the powerful Detroit Red Wings in four games.
3. 1985-86 Montreal Canadiens
While the 1986 Montreal Canadiens were a decent team, there were many other much stronger teams to expect a Stanley Cup out of in 1986. The Edmonton Oilers, Philadelphia Flyers, and Washington Capitals were all teams that were expected to make a good push. Like the 1991 Pittsburgh Penguins, the Canadiens encountered a fair bit of luck along the way. In the first round, the Canadiens dominated the Boston Bruins in a best-of-five, going 3-0 in the series. Following that, their luck became evident. The Hartford Whalers had upset the Adams Division winners, the Quebec Nordiques in the first round, sparing the Canadiens from facing them. The Canadiens put an end to Hartford’s dreams in a seven game series before starting the Eastern Conference finals. Here, the New York Rangers had upset both Philadelphia and Washington to make it to the finals. The Canadiens shut down the Cinderella run of the Rangers in five games to make it to the Finals, where, instead of the Edmonton Oilers, Montreal had to face the Calgary Flames, who had upset the Oilers in seven games during the Division finals. The Canadiens took the best-of-seven in five games to win their first Cup in seven years. Rookie, Patrick Roy led the way and was awarded the Conn Smythe Trophy.
2. 1994-95 New Jersey Devils
In the shortened 1994-95 season, the New Jersey Devils placed 5th in the Eastern Conference with a 22-18-8 record. Unlike some earlier teams, the Devils were upsetting teams the entire way along their run to the Stanley Cup. After beating the #4 seeded Boston Bruins in five games, the Devils faced the Pittsburgh Penguins, just three years removed from a Stanley Cup themselves. Despite the regular season point discrepancy, the Devils came out on top in a shocking 4-1 series win. The Devils would continue to one-up themselves by facing yet an even stronger team in the Philadelphia Flyers, with the Next One, Eric Lindros leading their team. The Flyers had 60 points during their season, a notably jump over the 52-point season of the Devils. The Devils finally had a bit more of a challenge, needing six games to knock off the Flyers. Last of all and greatest of all, the Devils went up against the superstar-studded Detroit Red Wings, who had led the NHL with 70 points in the shortened season. Unbelievably, the Devils swept these behemoths in four games to win their first ever Stanley Cup. Claude Lemieux’s goal-scoring explosion of 13 goals earned him the Conn Smythe.
1. 1937-38 Chicago Black Hawks
The 1937-38 Chicago Black Hawks were not a good team. They weren’t even average. They were terrible. Their 14-25-9 record only got them into the playoffs because the Detroit Red Wings somehow had two points less. They were by far the worst team to make the NHL playoffs. In the quarterfinals, the Black Hawks surprised many with a 2-1 victory over the Canadiens. In the late 30s, the Canadiens were not a good team, so this wasn’t the stunning upset it would’ve been in many eras, but Montreal was still expected to win the series. In the other match of the quarterfinals, the New York Americans had stunned the New York Rangers. As a result, the Black Hawks faced the Americans in the Semi-finals, who had the exact same point total of the Canadiens, creating another expected loss for the Black Hawks. The Hawks stunned the Americans in another shocking 2-1 series victory and all of a sudden, the “terrible” Chicago Black Hawks were in the Stanley Cup final. While the other side of the semi-finals had featured an upset victory for the Maple Leafs over the 1st place Bruins, Toronto was still Chicago’s toughest opponent yet. In an upset for the ages, the 14-25-9 Black Hawks beat the 24-15-9 Toronto Maple Leafs in four games by a series score of 3-1. The victory was so unexpected that the Stanley Cup wasn’t even in the building when Chicago won the game. The upset was complete.